Naphthalene-catalysed lithiation of N,N-diisopropylbenzamide and its methoxy derivatives

Add time:08/20/2019    Source:sciencedirect.com

The reaction of N,N-disubstituted benzamide derivatives 1 with lithium and a catalytic amount of naphthalene (4 mol %) in the presence of carbonyl compounds (Barbier-type conditions) led to the formation of the corresponding 3,4-dihydro-4-substituted benzamides 2. The presence of a 4-tert-butyl group in the starting benzamide changed the position of the electrophilic fragment to give the 3,4-dihydro-3-substituted amide 3. When the reaction was performed with the corresponding methoxybenzamides 7, only reductive demethoxylation took place, giving (by reaction with carbonyl compounds) the corresponding substituted benzamides 8.

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